NP-MRD: Showing NP-Card for 6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid (NP0254482)

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Record Information

Version

2.0

Created at

2022-09-07 18:39:21 UTC

Updated at

2022-09-07 18:39:21 UTC

NP-MRD ID

NP0254482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

Description

Calendulaglycoside E, also known as ladyginoside a, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid is found in Ladyginia bucharica and Polyscias fruticosa. Calendulaglycoside E is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306582D          

 56 62  0  0  0  0            999 V2000
   11.3804    3.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4410    3.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541   -2.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0935   -2.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3383    0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4818   -0.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7788    0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673    1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0528    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0528   -1.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6239   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252    1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1962   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252    1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9107   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1962    1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -2.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4818    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1962    1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3384   -1.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0528   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1936   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1936   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516   -1.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660   -1.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0515   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4805   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252    0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9107    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6239   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3384   -0.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4818   -0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673   -0.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9107    0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937   -2.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.7210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -1.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081    0.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660   -2.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4805    1.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0515    1.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252   -0.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3396    0.7540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -1.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950   -1.7210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -0.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4805   -0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 20  8  2  0  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 24  9  1  0  0  0  0
 25 11  1  0  0  0  0
 26 22  1  0  0  0  0
 27 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 29  1  0  0  0  0
 35 30  1  0  0  0  0
 37  1  1  0  0  0  0
 37  2  1  0  0  0  0
 37 14  1  0  0  0  0
 37 18  1  0  0  0  0
 38  3  1  0  0  0  0
 38  4  1  0  0  0  0
 38 23  1  0  0  0  0
 38 25  1  0  0  0  0
 39  5  1  0  0  0  0
 39 12  1  0  0  0  0
 39 23  1  0  0  0  0
 39 24  1  0  0  0  0
 40  6  1  0  0  0  0
 40 15  1  0  0  0  0
 40 20  1  0  0  0  0
 41  7  1  0  0  0  0
 41 13  1  0  0  0  0
 41 24  1  0  0  0  0
 41 40  1  0  0  0  0
 42 16  1  0  0  0  0
 42 17  1  0  0  0  0
 42 21  1  0  0  0  0
 42 36  1  0  0  0  0
 43 19  1  0  0  0  0
 44 26  1  0  0  0  0
 45 27  1  0  0  0  0
 46 28  1  0  0  0  0
 47 29  1  0  0  0  0
 48 30  1  0  0  0  0
 49 33  2  0  0  0  0
 50 33  1  0  0  0  0
 51 36  2  0  0  0  0
 52 36  1  0  0  0  0
 53 22  1  0  0  0  0
 53 34  1  0  0  0  0
 54 25  1  0  0  0  0
 54 35  1  0  0  0  0
 55 31  1  0  0  0  0
 55 34  1  0  0  0  0
 56 32  1  0  0  0  0
 56 35  1  0  0  0  0
M  END

     RDKit          3D

122128  0  0  0  0  0  0  0  0999 V2000
  -10.3152    1.2067    0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3447    0.0589    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6209   -0.6099    1.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5798   -0.8997   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6765   -2.0777   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2478   -1.7896   -0.1646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8135   -2.9837    0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5854   -2.8980    1.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6773   -4.1854    0.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4590   -1.7610   -1.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9665   -1.7530   -1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693   -0.4676   -0.4906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6417    0.6083   -1.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753   -0.1051    0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070    0.8079    1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    1.3881    1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679    0.3265    1.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1558   -0.6324    0.0418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1512   -2.0433    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -0.7258   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640   -0.0457   -1.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    1.2494   -0.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4339    1.8299   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221    1.5871   -1.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    3.3442   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4621    1.1678    0.3917 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.3170    2.2477   -0.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5325    0.1694   -0.7274 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0371   -0.6481    0.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3669   -2.9759    0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4859   -2.7133    1.6172 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4134   -1.9280   -1.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4925   -2.4695   -0.5497 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7420   -0.4666   -1.5648 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5121   -0.4995   -2.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3958    0.1279   -1.9203 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8914   -0.7483   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216    0.4433    0.8087 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6844    0.0816    1.7125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7396    1.4445    1.3238 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1176    0.9917    2.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1240   -1.5884    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3566   -0.3344   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6147   -1.2371   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0968   -2.7619    0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6948   -2.6237   -1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1832   -4.3881   -0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6999   -2.6891   -2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170   -0.9122   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952   -2.6648   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4720   -1.7401   -2.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976    0.1852   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8166    1.3108   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    1.2213   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300    1.0968    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7828    2.2262    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8068    2.2887   -2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    3.7799   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9019    3.8717   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798    3.6332    0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5585    0.5476   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8755    0.6330   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061306582D          

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M  END
> <DATABASE_ID>
NP0254482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OC(C(OC7OC(CO)C(O)C(O)C7O)C(O)C6O)C(O)=O)C(C)(C)C5CCC34C)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H66O14/c1-37(2)14-16-42(36(51)52)17-15-40(6)20(21(42)18-37)8-9-24-39(5)12-11-25(38(3,4)23(39)10-13-41(24,40)7)54-35-30(48)28(46)31(32(56-35)33(49)50)55-34-29(47)27(45)26(44)22(19-43)53-34/h8,21-32,34-35,43-48H,9-19H2,1-7H3,(H,49,50)(H,51,52)

> <INCHI_KEY>
OFLDMHFCMNKHGN-UHFFFAOYSA-N

> <FORMULA>
C42H66O14

> <MOLECULAR_WEIGHT>
794.965

> <EXACT_MASS>
794.44525682

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
86.6388559917186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.373436680000002

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.7683847036023375

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.476944967644412

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483775779257686

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
198.31850000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      21.243   5.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.223   5.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.221  -4.392   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.241  -4.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.565   0.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.566  -1.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.254   0.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.232   2.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.899   1.407   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.899  -3.213   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.898  -0.903   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.231  -0.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.232  -2.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.567   3.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.900  -0.903   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.567   2.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.233  -0.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.900   3.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.562  -4.753   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.566   1.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.900   2.177   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.562  -3.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.565  -2.443   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.899  -0.133   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.898  -2.443   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.228  -2.443   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.228  -0.903   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.563  -2.443   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.562  -0.133   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.897  -3.213   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.563  -0.903   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.897  -0.133   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.897   1.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.896  -0.903   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.230  -2.443   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.567   0.637   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.233   4.487   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.231  -3.213   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.565  -0.903   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.566  -0.133   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      18.232  -0.903   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      22.233   1.407   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.228  -5.523   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.895  -3.213   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.895  -0.133   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       6.229  -3.213   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       3.562   1.407   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       8.897  -4.753   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      10.230   2.177   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       7.563   2.177   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      23.567  -0.903   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      24.901   1.407   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       4.896  -2.443   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      11.564  -3.213   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       6.229  -0.133   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      10.230  -0.903   0.000  0.00  0.00           O+0
CONECT    1   37                                                            
CONECT    2   37                                                            
CONECT    3   38                                                            
CONECT    4   38                                                            
CONECT    5   39                                                            
CONECT    6   40                                                            
CONECT    7   41                                                            
CONECT    8    9   20                                                       
CONECT    9    8   24                                                       
CONECT   10   13   23                                                       
CONECT   11   12   25                                                       
CONECT   12   11   39                                                       
CONECT   13   10   41                                                       
CONECT   14   16   37                                                       
CONECT   15   17   40                                                       
CONECT   16   14   42                                                       
CONECT   17   15   42                                                       
CONECT   18   21   37                                                       
CONECT   19   22   43                                                       
CONECT   20    8   21   40                                                  
CONECT   21   18   20   42                                                  
CONECT   22   19   26   53                                                  
CONECT   23   10   38   39                                                  
CONECT   24    9   39   41                                                  
CONECT   25   11   38   54                                                  
CONECT   26   22   27   44                                                  
CONECT   27   26   29   45                                                  
CONECT   28   30   31   46                                                  
CONECT   29   27   34   47                                                  
CONECT   30   28   35   48                                                  
CONECT   31   28   32   55                                                  
CONECT   32   31   33   56                                                  
CONECT   33   32   49   50                                                  
CONECT   34   29   53   55                                                  
CONECT   35   30   54   56                                                  
CONECT   36   42   51   52                                                  
CONECT   37    1    2   14   18                                             
CONECT   38    3    4   23   25                                             
CONECT   39    5   12   23   24                                             
CONECT   40    6   15   20   41                                             
CONECT   41    7   13   24   40                                             
CONECT   42   16   17   21   36                                             
CONECT   43   19                                                            
CONECT   44   26                                                            
CONECT   45   27                                                            
CONECT   46   28                                                            
CONECT   47   29                                                            
CONECT   48   30                                                            
CONECT   49   33                                                            
CONECT   50   33                                                            
CONECT   51   36                                                            
CONECT   52   36                                                            
CONECT   53   22   34                                                       
CONECT   54   25   35                                                       
CONECT   55   31   34                                                       
CONECT   56   32   35                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
Ladyginoside a	HMDB
6-[(8a-Carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₄₂H₆₆O₁₄

Average Mass

794.9650 Da

Monoisotopic Mass

794.44526 Da

IUPAC Name

6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OC(C(OC7OC(CO)C(O)C(O)C7O)C(O)C6O)C(O)=O)C(C)(C)C5CCC34C)C2C1)C(O)=O

InChI Identifier

InChI=1S/C42H66O14/c1-37(2)14-16-42(36(51)52)17-15-40(6)20(21(42)18-37)8-9-24-39(5)12-11-25(38(3,4)23(39)10-13-41(24,40)7)54-35-30(48)28(46)31(32(56-35)33(49)50)55-34-29(47)27(45)26(44)22(19-43)53-34/h8,21-32,34-35,43-48H,9-19H2,1-7H3,(H,49,50)(H,51,52)

InChI Key

OFLDMHFCMNKHGN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ladyginia bucharica	LOTUS Database	35616633
Polyscias fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Pyran
Oxane
Dicarboxylic acid or derivatives
Fatty acyl
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.28	ALOGPS
logP	3.37	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	198.32 m³·mol⁻¹	ChemAxon
Polarizability	86.64 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0033174

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011183

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13919550

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid (NP0254482)

MOL for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0254482 (6-[(8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid)